3-Fluoro-4-trifluoromethyl-phenylboronic acid → (rac)-N-(4-(3-Fluoro-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

HRID 714080Notes

Reaction equation

HRID 714080 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[C:6]=2[CH:5]=[N:4][CH:3]=1.[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[C:24]([F:27])([F:26])[F:25]>>[F:17][C:18]1[CH:19]=[C:20]([C:2]2[C:11]3[CH2:10][CH2:9][CH2:8][CH:7]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[C:6]=3[CH:5]=[N:4][CH:3]=2)[CH:21]=[CH:22][C:23]=1[C:24]([F:25])([F:26])[F:27]

Participants

3

Reactant 2

HCID 177500503-Fluoro-4-trifluoromethyl-phenylboronic acidHCID 86685953N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

Product 1

HCID 71811698(rac)-N-(4-(3-Fluoro-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamideYield 80%

Procedure

In analogy to the procedure described for the preparation of example 1, (rac)-N-(4-bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide (intermediate A-1) was reacted with 3-fluoro-4-(trifluoromethyl)phenylboronic acid to give the title compound as light brown foam in 80% yield. MS: 367.1 (M+H+).

Sources & evidence

ORD record
ord-b5f6a94f70324e7fa4bc821d00ccae4d
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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